WO1996038406A1 - Phenylalkanamide derivatives and agrohorticultural bactericides - Google Patents

Abstract

Phenylalkanamide derivatives represented by general formula (1) and novel agrohorticultural bactericides containing the same as the active ingredient, wherein R1 represents hydrogen, alkyl, etc.; R?2, R3 and R4¿ represent each alkyl, hydrogen, etc.; Q represents cyano, carboxyl, etc.; X represents alkyl, alkoxy, halogeno, aryl, etc.; n represents an integer of 0 to 3; and Y and Z represent each alkyl, hydrogen, etc. The bactericides have a remarkably high preventive effect on rice blast, apple scab, and so forth without adversely affecting the crops, and excellent in permeability and translocatability, thus exhibiting a remarkably high control effect on rice blast in submerged application.

Description

 Specification

 Phenylalkanoic acid amide derivatives and fungicides for agricultural and horticultural use

 [Technical field]

 The present invention relates to a novel compound which is a novel compound not described in any literature, and a fungicide for agricultural and horticultural use containing the same as an active ingredient.

 [Background technology]

 To date, N- (1-cyano 1-cyclopropylethyl) 1-2- (2,4-dichloromouth phenyl) acetamides and other N-phenylacetaminotriles have been 3-aryl. It is known as an intermediate for the production of pyrrolidine-1,2,4-dione (JP-A-6-222004 and JP-A-6-263731). Its usefulness as an agricultural and horticultural fungicide is not known at all.

 In recent years, the use of agricultural and horticultural fungicides has led to the emergence of drug-resistant bacteria, and existing drugs may not show sufficient fungicidal activity. In addition, new L and fungicides that can efficiently control harmful bacteria at a low concentration are required due to environmental problems.

 The present inventors synthesized various novel phenylalkanoic acid amide derivatives in order to develop a drug having a bactericidal activity superior to conventionally known bactericides, and examined the physiological activities thereof. The present inventors have found that the compound has an excellent bactericidal activity against rice blast and the like and does not cause any harm to useful crops, thereby completing the present invention.

 "Disclosure of the invention"

 That is, the present invention relates to the general formula (1)

[In the formula, R ¹ represents a hydrogen atom or a C E -C ₆ alkyl group, R ² represents a hydrogen atom, C 1 ~ c ₆ alkyl group, C. It represents -C c cycloalkyl group or C丄-C Haroaruki group, R ³ and R ⁴ are independently C丄~ C ₆ alkyl group, C ₀ ~ c ₆ alkenyl group, C ₃ -C ₆ cycloalkyl group, C ₂ -C alkoxyalkylene Represent a group or C i to C ₄ haloalkyl group, or cycloalkyl group (in which the R ³ and R ⁴ are 5-membered to 7-membered ring together with the carbon atoms that are linked by C _sigma -C ₆ alkyl group Q may be a cyano group or a group C 0 R ^a (R ³ is a hydroxy group, a C i C alkyl group, a C i C alkoxy group, a C.-C haalkenyloxy) It represents groups, c ₂ ~ c ₆ Arukiniruokishi group, C.～C Hashikuro Arukiruokishi group, a phenoxy group, Benjiruokishi group, an amino group, a C ~ C ₆ § Rukiruami amino group or a C I～C Jiarukiruami cyano group.) X represents a halogen atom, a 丄 -alkyl group, a C ₀ -CP alkenyl group, Wa ~ Ji alkynyl group, c ₃ to c ₆ cycloalkyl group, C i~C ₄ Ha port alkyl group, arsenate Dorokishi group, C j C g alkoxy group, c ₂ to c ₆ Arukeniruokishi group, c ₂ ~ c ₆ alkynyloxy group, Co-c cycloalkyloxy group, di-, halo-alkoxy group, aryloxy group (the group is a C-c alkyl group, a di-, a-alkyl group, a di-alkyl group) Flip alkoxy group, Shiano group, may be substituted by nitro group or a halogen atom.), hetero § reel O alkoxy (in which the group C ~ C alkyl le group, ci ~ C haloalkyl group, c, ~ c ₆ It may be substituted by an alkoxy group, a cyano group, a nitro group or a halogen atom.) Alkylthio O group, C to c ₆ alkylsulfinyl group, C ~ C alkyl sulfonyl group,

C j~C j haloalkylthio group, § Li one thio group (said group c _x ~ c ₆ alkyl groups, C E to c 4 haloalkyl group, Ji, ~ Haarukokishi group, Shiano group, nitro group or halogen atom May be substituted.), A heteroarylthio group (the group is a C 丄 -C haalkyl group, a c ， -C haloalkyl group, a CiC alkoxy group, a cyano group, a nitro group or a halogen atom. but it may also be substituted.), § Li one Rusurufiniru (in which the group C I～C alkyl group, C i~C ₄ Ha port alkyl group, C i C g alkoxy group, Shiano group, a nitro group, or May be substituted by a halogen atom.), An arylsulfonyl group (the group may be a C ₆ -C ₆ alkyl group, a C 丄 -C ₄ alkyl group, a C Ce alkoxy group, a cyano group, May be substituted by a group or a halogen atom ), Amino group, C j -C Arukiruami amino group, C j ~ c ₆ dialkyl amino group, a nitro group, Shiano group, Ariru (in which the group c丄to c ₆ alkyl group, c ₁ to c ₄ Haguchi alkyl group, ^c i to ^c e alkoxy group, Shiano group, may be substituted by nitro group or a halogen atom. ), Heteroariru (in which the group c丄to c ₆ alkyl group, c: ~ c 4 haloalkyl groups, C i C g alkoxy group, Shiano group, may be substituted by a nitro group or a halogen atom). An aralkyl group (the group may be substituted by a ci-calkyl group, a c, -c4 haloalkyl group, a c-c alkoxy group, a cyano group, a dinitro group or a halogen atom); Le carbonyl group, § reel carbonyl group (said group c丄~ c ₆ alkyl group,.丄~ haloalkyl group, CC Haarukokishi group, Shiano group, may be substituted by two Toro group or halogen atom.) , hetero § reel carbonyl group (said group Ci～C p alkyl group, .c丄~ c ₄ haloalkyl groups, C i~c ₆ alkoxy group, Shiano group, optionally substituted by nitro group or a halogen atom There.), Represents a formyl group or a C _chi ~ C alkoxycarbonyl two Le group, Y and Z are each hydrogen atom, C, ~ CP alkyl group, C, -C haloalkyl group, C i ~ C Haaru Kokishi group, Shiano Represents a group, a nitro group or a halogen atom, and n represents an integer of 0 to 3. However, when R ¹ and R ² simultaneously represent a hydrogen atom, Y and Z both represent a hydrogen atom, and n represents an integer of 1 to 3. And (2) a fungicide for agricultural and horticultural use containing the funilyl alkanoic acid amide derivative as an active ingredient.

The terms used in this specification will be described below. In this specification, for example, notations such as “C j to C ₆ ” indicate that the number of carbon atoms of the substituent following this is 1 to 6 in this case.

The C. 1 to ^c ₆ alkyl group, a linear or represents a branched chain alkyl group, for example, methylation group, Echiru group, n- propyl group, an isopropyl group, n - butyl group, Isopuchi Le group, sec- butyl Group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, isohexyl group, 3,3-dimethylbutyl group and the like.

C ₃ A -C ₆ consequent opening alkyl group is, for example, cyclopropyl group, consequent opening pentyl group, cyclohexylene a cyclohexyl group.

A C 1 -C haloalkyl group is a straight-chain or It represents a branched alkyl group, and examples thereof include a fluoromethyl group, a chloromethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, and a pentafluoroethyl group.

The c ₂ -c ₆ alkenyl group represents a linear or branched alkenyl group, for example, a vinyl group, a 1-propenyl group, an aryl group, an isopropyl group, a 1-butenyl group, a 2-butenyl group. And the like.

The term “c ₂ -c ₆ alkynyl group” means a linear or branched alkynyl group, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, Examples thereof include a 3-butynyl group, a 4-methyl-1-pentynyl group, and a 3-methyl-1-pentynyl group.

 Examples of the aryl group include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.

 Heteroaryl groups are, for example, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, 3-furyl, 2-phenyl, 3-phenyl, 3-phenyl, 1-pyryl, Examples thereof include a 2-pyrrolyl group and a 3-pyrrolyl group.

An aralkyl group refers to a straight-chain or branched C i -C ₃ alkyl group substituted by an aryl group (having the above-mentioned meaning), for example, a benzyl group, a phenyl group, a 1-naphthylmethyl group, Examples thereof include a 2-naphthylmethyl group. The halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The C i -C p alkoxy group represents a linear or branched alkoxy group, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec —Butoxy group, tert-butyne group, n-pentyloxy group, isopentyloxy group, n-hexyloxy group and the like.

The term “c ₂ -c ₆ alkenyloxy group” means a linear or branched alkenyloxy group, and examples thereof include an aryloxy group, an isopropyloxy group, and a 2-butenyloxy group.

The term “c ₂ -c ₆ alkynyloxy group” means a linear or branched alkynyloxy group, for example, 2-propynyloxy group, 2-butynyloxy group, 3-butynyl And the like.

The c ₃ to c ₆ cycloalkyl O alkoxy group, may be mentioned for example, cyclopropyl O alkoxy group, cyclo pentyl Ruo alkoxy group, a Kishiruokishi group to consequent opening.

 The C j -C haloalkoxy group represents a straight-chain or branched-chain alkoxy group substituted by a halogen atom, for example, a fluoromethyoxy group, a difluoromethyoxy group, a trifluoromethoxy group, a pentafluoroethoxy group. And the like.

 Examples of the aryloxy group include a phenoxy group, a 1-naphthyloxy group and a 2-naphthyloxy group.

 The heteroaryloxy group i is, for example, a 2-pyridyloxy group, a 3-pyridyloxy group, a 4-pyridyloxy group, a 2-furyloxy group, a 3-furyloxy group, a 2-phenyloxy group, a 3-phenyloxy group, or the like. Can be mentioned.

 The aralkyloxy group represents a linear or branched C i -C alkoxy group substituted by an aryl group, and examples thereof include a benzyloxy group and a phenethyloxy group.

The C ₇ -C alkylthio group represents a linear or branched alkylthio group, for example, a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, a sec-butylthio group, Examples thereof include a tert-butylthio group and an n-hexylthio group.

 The C1-C6 alkylsulfinyl group means a linear or branched alkylsulfinyl group, for example, a methylsulfinyl group, an ethylsulfinyl group, an n-butylpyrusulfinyl group, an isopropylsulfinyl group, an n-butylsulfinyl group Groups, isobutylsulfinyl group, sec-funanoresnorefininole, tert-butylsulfinyl group, n-hexylsulfinyl group and the like.

The C i -C ₆ alkylsulfonyl group means a straight chain or branched alkylsulfonyl group, for example, methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropylsulfonyl group, _n- butylsulfonyl group Group, isobutylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group, n-hexylsulfonyl group and the like. The C j~c ₄ haloalkylthio group, substituted by a halogen atom, a straight-Zhen or an branched alkylthio groups, for example, full-O b methyl thio group, Jifuruo Romechiruchio group, triflate Ruo b methylthio group, pen evening full Oloethylthio group and the like.

 Examples of the arylthio group include a phenylthio group, a 1-naphthylthio group, and a 2-naphthylthio group.

 A heteroarylthio group is, for example, a 2-pyridylthio group, a 3-pyridylthio group, a 4-pyridylthio group, a 2-furylthio group, a 3-furylthio group, a 2-cyenylthio group, a 3-chenylthio group, or the like. Can be mentioned.

 Examples of the phenylsulfinyl group include a phenylsulfinyl group, a 1-naphthylsulfinyl group, a 2-naphthylsulfinyl group and the like.

 The arylsulfonyl group includes a phenylsulfonyl group, a 1-naphthylsulfonyl group, a 2-naphthylsulfonyl group and the like.

The C 1 -c ₆ alkylamino group represents a linear or branched alkylamino group, for example, a methylamino group, an ethylamino group, an n-propylamino group, an isopropylamino group, and an n-butylamino group. And an isobutylamino group, a sec-butylamino group, a tert-butylamino group, an n-hexylamino group and the like.

 Examples of the C, to C hadialkylamino group include a dimethylamino group, a getylamino group, a dipropylamino group, a dibutylamino group, and the like.

The C j~C ₆ alkylcarbonyl group, a straight-chain or branched alkyl carbonylation group, for example Asechiru group, a propionyl group, Puchiriru group, can be exemplified Isobuchiriru group.

 Examples of the arylcarbonyl group include a benzoyl group, a 1-naphthylcarbonyl group, and a 2-naphthylcarbonyl group.

Heteroarylcarbonyl groups include, for example, 2-pyridylcarbonyl group, 3-vinylidylcarbonyl group, 4-pyridylcarbonyl group, 2-furylcarbonyl group, 3-furylcarbonyl group, 2-phenylcarbonyl group, and 3-— And a phenylcarbonyl group. The c. 1 to ^c ₆ alkoxycarbonyl group, a straight-chain or represents branched Arukokishikaru Boniru groups such main Bok alkoxycarbonyl group, an ethoxycarbonyl group, n- flop port Po alkoxycarbonyl group, isopropoxycarbonyl radical, n —Butoxycarbonyl group, isobutoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, n-pentyloxycarbonyl group, n-hexyloxy group, etc. it can.

 Some of the compounds of the present invention represented by the general formula (1) have one or more asymmetric carbon atoms in the molecule, and such compounds have optical isomers. Pure individual diastereomers, enantiomers and mixtures thereof are also included in the compounds of the present invention.

Preferred compounds of the present invention compound represented by the general formula (1), but a hydrogen atom or a methyl group, R ² is a hydrogen atom, a methyl group or an Echiru group, R ^Y is methyl group, Echiru group or η- R ⁴ is methyl, ethyl, η-propyl, isopropyl, η-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclopentyl, or dichloromethyl And Q is a cyano group, a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an isopropoxycarbonyl group, an n-butoxycarbonyl group, a sec-butoxycarbonyl group or a carbamoyl group, and X is a fluorine atom. , Chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, isopropyl group, isobutyl group, sec-butyl group, tert-butyl group Group, cyclopentyl group, cyclohexyl group, trifluoromethyl group, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, difluoromethyoxy group, trifluoromethoxy group, phenoxy group, methylthio group, An ethylthio group, an isopropylthio group, a dimethylamino group, a getylamino group, a nitro group, a cyano group, a phenyl group, an acetyl group or a benzoyl group, Y and Z are a hydrogen atom or a fluorine atom, and n is an integer of 1 to 3 And the following compounds can be mentioned.

Next, Tables 1 to 24 show typical examples of the compound of the present invention represented by the general formula (1), but are not limited thereto. The compound number will be referred to in the following description. The symbols in the table represent the following meanings. Me represents a methyl group, Et represents an ethyl group, Pr—n represents an n-propyl group, Pr—i represents an isopropyl group, and Bu—n represents n— Represents a butyl group, Bu-i represents an isobutyl group, Bu-s represents a sec-butyl group, But represents a tert-butyl group, and Pr-cyc represents a cyclobutyl group. Represents a propyl group, Pen-eye represents a cyclobenzyl group, Ph represents a phenyl group, and 4-OP h (2-C 1) represents 4- (2-chlorophenyl). 4-0 (2-Py) represents a 4- (2-pyridyl) oxy group, and 4-0 (5-CFo, 2-Py) represents a 4- (5 Trifluoromethyl-2-pyridyl) oxy group, 4-0 (3-Py) represents a 4- (3-pyridyl) oxy group, and 410 (4-Py) represents 4-1 ( Represents a 4-pyridyl) oxy group, and 4—S Ph (2-C 1) It represents Chio group, 4- S (0) P h (2 -C 1) and represents a 4- (2-black port phenyl) sulfinyl _{group, 4- SO n Ph (2 -C} 1) and 4 one represents (2-black port Hue sulfonyl) sulfonyl Le group, 4- S (2 - P y) and represent 4- (2-pyridyl) Chio group, 4 one P h (4 - CF ₃₎ the 4- (4-trifluoromethylphenyl) group, 4- (2-Py) represents 4- (2-pyridyl) group, and 4- (2-Fur) is 4- ( (2-furyl) group, 4- (2-Thi) represents 4- (2-phenyl) group, 4-COPh (2-Me) is 4- (2-methylbenzoyl) 4—CO (3-Py) represents a 4- (3-pyridyl) carbonyl group, and 4-—CO (2-Fur) represents a 4- (2-furyl) carbonyl group. It represents, 4- CO (2-T hi) and represents 4 one (2-thienyl) carboxamide two Le _{group, 4 - CH 2 P h (} 3 - C 1) and 4- (3-black port benzylidene ) Group, the 4- (1 _ P Yrr) represents a 4- (1-pyrrolyl) group.

(Halla) O / 96df / I3d 8Ε / 96 OAV (Table 2)

Compound

Xn R ³ R ⁴ Melting point (° C) No.

A-27 4-Br Me CHC1 ₂

 A-28 4-ΒΓ Et Et

 A-29 4- Br Et Pr-i

 A-30 4-1 Me Pr-i 125-126

A-31 3, 4- Cl ₂ Me Pr-i 139-140

A-32 3.5-Cl ₂ Me Pr-i

 A-33 4-Me Me Pr-i 100-101

A-34 4-Et Me Pr-i 104-105

A-35 4-Pr-i Me Pr-i 70-71

A-36 4-Bu-i Me Pr-i

 A-37 4-C≡CMe Me Pr-i

 A-38 4-CH = CHMe Me Pr-i

 A-39 4-Bu-t Me Pen-cyc

 A-40 4-Bu-t Me

^CF 3

 A-41 4-Bu-t Me Pr-i 97- 98

A-42 4- Pen-eye Me Bu-i

 A-43 4-Bu-t Me Bu-s

 A-44 4-Bu-t Me CH ゥ OMe

 A- 45 4-Bu-t Et Et

 A-46 4-Bu-t Et Pr-n

 A-47 4-Bu-t Et Pr-i

A-48 4-CF ₃ Me -CH CH = CH _n

 A-49 Me Et

A-50 4-CF ₃ Me Pr-n

A-51 4-CF ₃ Me Pr-cyc

A-52 4-CF ₃ Me Pr-i 104-105

A-53 4- CF ₃ Me CHC1 ₂

 A-54 Me Bu-i 94- 96

⁴ — ^CF 3

 A-55 Me Bu-s

⁴ one ^CF 3

A-56 4- CF ₃ Me Bu-t 166-167 (Table 3)

Compound

 Xn R R. Melting point (.C) number

A- 57 4-CF, Et Et 100-102 A- 58 4- CF; Et Pr-n

A-59 4- CF: Me Pr- A- 60 4-OH Me Pr- 152-153 A- 61 4-O e Me Pr- 107-108 A- 62 4-OEt Me Pr-96-97 A-63 4-OPr-i Me Pr- 76- 77 A- 64 4-OBu-n Me Pr-98- 99 A- 65 4-0CH CH = CH ₂ Me Pr- A- 66 4-0CH C≡CH Me Pr- A-67 4-OPen-cyc Me Pr-A-68 4-0CF. Me Pr- 85- 86 A- 69 4-0CF ₃ Me Bu-i

A- 70 4-0CF ₃ Me Bu-s

A- 71 4-0CF ₃ Me Bu-t 152-154 A- 72 4-0CF Me

^CF 3

A-73 4-0CF _r Et Et

 A- 74 3, 4- (0Me) Me Pr-89- 90 A- 75 3, 4, 5- (0Me) Me Pr- 82- 83

 Three

A- 76 4-OPh Me Pr- 139-141 A- 77 4-0 (2- Py) Me Pr- A- 78 4- 0 (5- CF ₃ , 2- Py) Me Pr- 132-133 A- 79 4-0 (3-Py) Me Pr- A- 80 4-0 (4-Py) Me Pr- A- 81 4-SMe Me Pr - 122-123 A- 82 4 - S0 2 Me Me Pr- 116 -118 A- 83 4-SPh Me Pr- A- 84 4-S0 ₂ Ph Me Pr- A- 85 4-NH Me Pr-

Two

A- 86 4-N (Me) Me Pr-i 147-148 (Table 4) Compounds

Xn R ³ R ⁴ Melting point (° C) No.

A-87 4-Ph Me Pr-i 151-152

A-88 4-S (2-Py) Me Pr-i

 A- 89 4-S (4-Py) Me Pr-i

 A-90 4-Ph Me Bu-s

 A-91 4-Ph Me Bu-t

 A-92 4-Ph Et Et 169-170

A-93 4-Ph (4-CF ₃ ) Me Pr-i

 A-94 4-Ph (2-CN) Me Pr-i

A- 95 4-Ph (3- N0 2) Me Pr-i

 A-96 4-Ph (4- CI) Me Pr-i

 A-97 4-Ph (4-Me) Me Pr-i

 A-98 4-Ph (4-0Me) Me Pr-i

 A-99 4-(2-Py) Me Pr-i

 A-100 4- (3-Py) Me Pr-i

 A-101 4-(4- Py) Me Pr-i

 A-102 4-(2- Fur) Me Pr-i

 A-103 4- (2-Thi) Me Pr-i

 A-104 4- CN Me Pr-i 126-127

A-105 Me Pr-i 135-136

A-106 4-COMe Me Pr-i

 A-107 4-COPh Me Pr-i 106-108

A-108 4- C0Ph (2-Me) Me Pr-i

 A-109 4-C0Ph (3-0Me) Me Pr-i

 A-110 4- C0Ph (4- CI) Me Pr-i

 A-111 4- CO (2- Fur) Me Pr-i

A-112 4_f0 C2-Thi) p _r -i

 A- 113 4-C0 (3-Py) Me Pr-i

 A-114 4-C0 Me Me Pr-i

A- 115 4-CH ₂ Ph Me Pr-i

A-116 4-CH ₂ CH ₉ Ph Me Pr-i

A- 117 4-1 Me Bu-t 170-172 (Table 5)

化合物

Compound

Xn R ³ R ⁴ R ⁵ Melting point (° C)

B- 1 3-C1 Me Pr-i OMe

 B- 23-Me Me Pr-i OMe

 R D- o 3-OMe Me Pr2 i OMe

R— A * ± 3-CF ₃ Me Pr-i OMe

 D D_

 o 3-NO Me Pr-i OMe

 R D- R υ 4-C1 Me Pr-i OMe 142-143

B-7 4-C1 Me Pr-i OEt 107-109

B-8 4-C1 Me Pr-i OPr-i 111-112

B-q 4- CI Me Pr-i OCH „Ph

D in 4-CI Me Pr-i OCH CH = CH ₂

 D 4-C1 Me Pr-i OCH C CH

 R u- 1 9 4-C1 Me Pr-i OPh

B- 13 4-C1 Me Pr-i NH ₂ 203-204

B- 14 4-CI Me Pr-i N (Me) ₂

 B- 15 4- CI Me Pr-i Me

 B- 16 4-C1 Et Et OMe

 B-17 4- CI Et Et OEt

 B-18 4- CI Et Et OPr-i

 B- 19 4-C1 Et Et 0CH Ph

B- 20 4- CI Et Et 0CH CH = CH ₂

B- 21 4- CI Et Et OCH ₂ C≡CH

 B-22 4- CI Et Et OPh

B- 23 4- CI Et Et H ₂

 B- 24 4- CI Et Et N (e)

 B- 25 4-CI Et Et Me

B- 26 4- CI Me Bu-t OMe (Table 6)

(表 7 )

(Table 7)

Compound

Xn R ⁴ R ⁵ Melting point (° c) No.

B- 57 Me Bu-t OCH C≡CH

⁴ " ^CF 3

B- 58 4- CF ₃ Me Bu-t NH ₂

B-59 4-CF ₃ Me Bu-t Thigh e

B-60 4- CF ₃ Me Bu-t Pr-i

 B- 61 4-Bu-t Me Pr-i OMe

 B- 62 4-Bu-t Me Pr-i OEt

B- 63 4-Bu-t Me Pr ^: i OPr-i

 B- 64 4-Bu-t Me Pr-i 0CH P

B-65 4-Bu-t Me Pr-i OCH CM ₂

B-66 4-Bu-t Me Pr-i OCH ₀ C≡CH

 B-67 4-Bu-t Me Pr-i OPh

B- 68 4-Bu-t Me Pr-i NH ₂

 B-69 4-Bu-t Me Pr-i cold e)

 B-70 4-Bu-t Me Pr-i Me

 B- 71 4-Bu-t Et Et OMe

 B-72 4-Bu-t Et Et OEt

 B-73 4-Bu-t Et Et OPr-i

B-74 4-Bu-t Et Et NH ₂

 B- 75 4-Pr-i Et Et OMe

 B-76 4-Pr-i Et Et OEt

 B- 77 4-Pr-i Et Et 2

B- 78 4-Pr-i Et Et N (Et) ₂

 B- 79 4-Pr-i Me Pr-i OMe

 B-80 4-Pr-i Me Pr-i OEt

 B- 81 4-Pr-i Me Pr-i OPr-i

B-82 4-Pr-i Me Pr-i NH ₂

 B- 83 4-Pr-i Me Pr-i Me

 B-84 4-Br Me Pr-i OMe

 B-85 4-Br Me Pr-i OEt

B-86 4-Br Me Pr-i OPr-i (Table 8)

Compound

Xn R ³ R ⁴ R ⁵ mp ⁽⁰ c) number No.

B-87 4- Br Me Pr-i OCH ヮ Ph

 B-88 4- Br Me Pr-i OCH ゥ CH = CH.

B-89 4-Br Me Pr-i 0CH ₉ C≡CH

 B- 90 4-Br Me Pr-i OPh

B- 91 4- Br Me Pr-i ₂

 B- 92 4-Br Me Pr-i N (Me)

 B-93 4-Br Me Pr-i Me

 B-94 4-Br Et Et OMe

 B-95 4-Br Et Et OEt

 B-96 4-Br Et Et OPr-i

 B- 97 4-Br Et Et OPen-cyc

B- 98 4-Br Et Et 0CH _o CH = CH ₂

 B-99 4-Br Et Et NHPr-i

B-100 4-Br Et Et NH ₂

 B-101 4-Br Et Et Me

 B-102 4-Br Me Bu-t OMe

 B-103 4-Br Me Bu-t OEt

 B-104 4-Br Me Bu-t OPr-i

 B-105 4-Br Me Bu-t OPen-cyc

B-106 4-Br Me Bu-t NH ₂

 B-107 4-Br Me Bu-t hall e

 B-108 4-Br Me Bu-t Me

 B-109 4-OMe Me Pr-i OMe

 B-110 4-OMe Me Pr-i OEt

 B-111 4-OMe Me Pr-i OPr-i

 B-112 4-OMe Et Et OEt

 B-113 4-OMe Et Et OPr-i

 B-114 4-Ph Me Pr-i OMe

 B-115 4-Ph Me Pr-i OEt

B-116 4-Ph Me Pr-i OMe 153-154 (Table 9)

(表 1 0 )

(Table 10)

CN

 Compound Melting point CO

Xn YR ³ R ⁴ or

 Refractive index (nj ^ u)

C-1-H Me Me 132-133

C-2-H Me Pr-eye 71-73

C-3-H Me Pr- i 108-110

C-4-H Et Et

 C-5-CI Me Pr- i

 C-6-Me Me Pr-i

 C-7-OMe Me Pr-i

 C-8-Me Pr-i

^CF 3

 C-9 one CN Et Et

C-10-N0 ₂ Et Et

 C-11-Me Et Et

 C-12 4-C1 F Me Pr-i

 C-13 4-C1 CI Me Pr-i 129-130

C-14 4-C1 CI Et Et

 C-15 3-F H Me Pr-i

 C-16 3-C1 H Me Pr-i 1.5 115

C-17 3-Br H Me Pr-i 1.5242

C-18 3-Me H Me Pr-i 71- 72

C- 19 3- Me H Me Pr-i 74- 76

C-20 3-0Me H Me Pr-i

C-21 3-CF ₃ H Me Pr-i 1.4660

C-22 3- CF ₃ H Me Pr-i 124-125

_{C- 23 3-N0 2 H Me} Pr-i

 C-24 3-COPh H Me Pr-i 117-119

C-25 3-COPh H Me Pr-i 1.5550

C-26 3- CH ₂ Ph H Me Pr-i (Table 11)

Compound Melting point (.c)

Xn YR ³ R ⁴ or numbered refractive index (n _D ^U)

C- 27 4-F H Me Pr-i 127-129

C- 28 4-F H Me Pr-i 124-127

C- 29 4-C1 H Me Me 148-149

C - 30 4 - C1 H - (C) 4 - 123-124

C- 31 4-C1 H Me Pr-n

 C- 32 4-C1 H Me Pr-cyc 1.5318

C-33 4-C1 HMe Pr-i 102-106

C- 34 4-C1 H Me p _r -i 125 -126

C- 35 4-C1 H M Pr-i 133-134

C- 36 4-C1 H Me CF

 C- 37 4-C1 H Me Bu-s

 C- 38 4-C1 H1.5141

C- 39 4-C1 H MP 122-124

C-40 4-C1 H Me Bu- 1 158-159

C- 41 4-C1 H Et Et 77- 79

C- 42 4-C1 H Et Et 77- 79

C-43 4-C1 H Et Et 77-79

C-44 4-C1 H Et Pr-i 90- 93

C- 454-Br H Me Pr-n

 C- 46 4- Br H Me Pen-cyc

 C- 47 4-Br H Me Pr-i 130-131

C-48 4- Br H Me Pr-i 121-123

C- 49 4-Br H Me Pr-i 87- 89 shi-bU 4-Br u Π Me Bu-s

 C- 51 4-Br H Me Bu- 1 143-144

C-52 4-Br H Me Bu-t 150-152

C- 53 4-Br H Et Et 97- 99

C- 54 4-1 H Me Pr-i 116-118

C- 55 4-1 H Me Pr-i 120-122

C- 56 4-1 H Me Pr-i 95- 98 (Table 1 2)

/:一

/:one

(Table 14)

Compound Melting point (° c)

 „3 ^ 4

 Xn Y R R or

? n index (n _D )

C-117 4-0CH ₂ GF ₃ H Me Pr-i 68- 70

C-118 4-0CH ₂ CF ₃ H Me Pr-i 98-101

C-119 4-OPr-i H Et Et 90- 93

C-120 4-OPr-n H Me Pr-i 105-107

C-121 4-OPen-cyc H Me Pr-i 108-110

C-122 H Me Pr-i 97-98

⁴ — ^0CF 3

C-123 4-0CF ₃ H Me Pr-i 122-124

C-124 4- 0CF ₃ H Me

^CF 3

 C-125 H Et Et 1.4776

⁴ Ichi ^{0 CF} 3

C-126 4-0CF ₃ H Me Bu-t

C-127 3.4- (0Me) ₂ H Me Pr-i

 C-128 3. 4, 5- (0Me) H Me Pr-i

 C-129 4-OPh H Me Pr-i 120-122

C-130 4-OPh H Me Pr-i 129-131

C-131 4-SMe H Me Pr-i

 C-132 4-S (0) Me H Me Bu-t

 C-133 4-SPr-i H Et Et

 C-134 4-SPh H Me Pr-i

C-135 4-S0 ₂ Me H Me Pr-i

C-136 4-S0 ₂ Ph H Me Pr-i

C-137 4- NH ₂ H Me Pr-i 1.5364

C-138 4-N (Me) ₂ H Me Pr-i

 C-139 4-NHPr-i H Me Pr-i

C-140 4-Ph H Me p _r -i 142-143

C-141 4-Ph H Me Pr-i 149-150

C-142 4-Ph H Et Et

 C-143 4-Ph H Me Bu-s

 C-144 4-Ph H Me Bu-t

 C-1 5 4-OPh (2- CI) H Me Pr-i

C-146 4-CH ₂ Ph (3-Cl) H Me Pr-i (Table 15)

Compound Melting point (° C)

Xn YR ³ R ⁴ or Ban refractive index _(eta ^upsilon)

C-147 4-Ph (4-Cl) H Me Pr-i

 C-148 4-Ph (2- Me) H Me Pr-i

 C-149 4-0Ph (3-Me) H Me Pr-i

C-150 4-CH ₉ Ph (4-Me) H Me Pr-i

 C-151 4-CH Ph (2-0Me) H Me Pr-i

 C-152 4-Ph (3-0Me) H Me Pr-i

 C-153 4-OPh (4-OMe) H Me Pr-i

 C-154 4- (2-Py) H Me Pr-i

 C-155 4- (3-Py) H Me Pr-i

 C-156 4- (4-Py) H Me Pr-i

 C-157 4-CN H Me Pr-i 148-149

C-158 4-CN H Me Pr-i 124-125

C-159 4- N0 ₂ H Me Pr-i 121-123

C-160 4-CO e H Me Pr-i

 C-161 4-COPh H Me Pr-i 105-108

C-162 4-COPh H Me Pr-i 154-157

C-163 4- C0Ph (3-Me) H Me Pr-i

 C-164 4-COPh (4-C1) H Me Pr-i

 C-165 4-C0 (2-Thi) H Me Pr-i 144-146

C-166 4-C0 (2-Thi) H Me Pr-i 115-117

C-167 4-C0 „Me H Me Pr-i

 C-168 4-C0 Pr-i H Me Pr-i

C-169 3, 4-Cl ₂ H Me Pr-i 100-102

C-170 3, 4-01 ^ H Me Pr-i 171-173

C-171 3, 4-Clo H Me Bu-t 134-136

C-172 3, 4-Cl ₂ H Me Bu-t 157-158

C-173 3. 4-Cl H Et Et 61- 63

C-174 3- CI, 4-OMe H Me Pr-i 1.5260

C-175 3- CI, 4-OMe H Me Pr-i 125-127

C-176 3-Cl, 4-OMe H Me Pr-i 88- 90 (Table 16)

Compound Melting point (° C) n YR ³ R ⁴ or Number Refractive index ( _n∑) ^{2 ()} )

C-177 3, 4- (Me) „H Me Pr-i 100-101

 L

C-178 3, 4- (Me) ₉ H Me Pr-i 128-130

 Two

 C-179 3, 4-(Me H Me Bu

 C-180 3, 4- (Me), H Me Bu-t 100-101

 Two

 C-181 4-C≡CMe H Me Pr-i 106-108

C-182 4-C3 CMe H Me Pr-i 78-80

C-183 4-CH = CH ₀ H Me Pr-i

 C-184 4-SMe H Me Bu-t 91- 94

C-185 4-SMe H Me Bu-t 108-110

C-186 4-SMe H Et Et 77- 78

C-187 4-1 H Me Bu-t 129-130

C-188 4-1 H Me Bu-t 132-133

C-189 4-1 H Me Pr-cyc 118-120

C-190 4-1 H Me Pr-cyc 142-144

C-191 4-1 H Et Et 105-108

C-192 4-0CF _Q H Me Bu-t 116-119

 Three

 C-193 4-(1-Pyrr) H Me Pr-i 119-120

C-194 4- (1- Pyrr) H Me Pr-i 156-158

C-195 4- (1-Pyrr) H Me Pr-i 123-125--iiJb 4-1 1 nl Mie rr l 102-104

C-197 4- CI H Me Pr-i 120-121

C-198 4-C1 H Me Pr-i 107-109

C-199 4-CI H Me Pr-i 121-122

C-200 4-OMe H Me Bu-t 1.5219

C-201 4-OMe H Me Bu-t 88- 90

C-202 4-OMe H Me Bu-t (Table 17)

COR ⁵

 Compound Melting point

Xn YR ° R ⁴ R No. ⁵ (.c)

D- 1-H Me Pr-i OMe

 D- 2-H Me Pr-i OEt

 D-3-H Me 'Pr-i OPr-i

D-4-H Me Pr-i NH ₂

 D-5-F Me Pr-i OMe

 D- 6 One CI Me Pr-i OMe

 D- 7 4-C1 F Me Pr-i OMe

 D-8 4-C1 CI Me Pr-i OMe

 D-9 3-Me H Me Pr-i OMe

 D-10 3-Me H Me Pr-i OEt

 D-11 3-Me H Me Pr-i OPr-i

 D- 12 3-Me H Me Pr-i N¾

 D-13 3- CI H Me Pr-i OMe

 D- 14 3-CI H Me Pr-i OEt

 D-15 3-C1 H Me Pr-i OPr-i

 D-16 3-CI H Me Pr-i NHg

_{D- 17 3-N0 2 H Me} Pr-i OMe

 D- 18 4-F H Me Pr-i OMe

 D-19 4- CI H Me Pr-i OMe 120-123

D-20 4-C1 H Me Pr-i OEt 115-118

D-21 4-C1 H Me Pr-i OPr-i 124-126

D-22 4-CI H Me Pr-i 0CH ₂ Ph

D-23 4-CI H Me Pr-i 0CH ₂ CH = CH

D-24 4-CI H Me Pr-i 0CH ₂ C≡CH

 D-25 4-C1 H Me Pr-i Me

D-26 4-CI H Me Pr-i NH ₂ 136-137 (Table 18)

Compound Melting point

Xn YR ⁴ R ^b number CO

D- 27 4-C1 H Me Pr-i N (Me) ₂

 D-28 4-C1 H Et Et OMe 98- 99

D- 29 4-C1 H Et Et OEt 85- 87

D-30 4-C1 H Et Et OPr-i

 D-31 4-C1 H Et Et Me

D-32 4-C1 H Et Et NH ₂ 116-118

D-33 4-C1 H Et Et N (Me) ₂

 D-34 4-C1 H Me Bu-t OMe 122-123

D-35 4-C1 H Me Bu-t OEt

 D-36 4-C1 H Me Bu-t OPr-i

 D- 37 4-C1 H Me Bu-t Me

D-38 4-C1 H Me Bu-t NH ₂

 D-394-Br H Me Pr-i OMe 124-126

D-40 4- Br H Me Pr-i OEt 92-94

D- 414-Br H Me Pr-i OEt 140-142

D-42 4-Br H Me Pr-i NH ₂ 132-134

D- 43 4-Br H Me Bu-s OMe

 D-44 4- Me H Me Pr-i OMe 76- 77

D- 45 4-Me H Me Pr-i OEt

 D-46 4- Me H Me Pr-i OPr-i

D- 47 4-Me H Me Pr-i 0CH ₂ Ph

 D-48 4-Me CI Me Pr-i OMe

 D-49 4-Me H Me Pr-i OPen-cyc

 D-50 4-Me H Me Pr-i Me

D-51 4-Me H Me Pr-i NH ₂ 140-146

D- 52 4-Me H Me Pr-i N (Me) ₂

 D- 53 4-Me H Et Et OMe

 D-54 4-Me H Et Et OEt

 D-55 4-Me H Et Et OPr-i

D- 56 4-Me H Et Et Me LZ

(6 I ¾) lfI0 / 96df / XDd 90fr8 € / 96O (Table 20)

(Table 22)

Compound

Xn YR ³ R ⁴ R ⁵ No. (.c)

D-146 3, 4-Cl H Me Pr-i OMe

 D-147 3, 4-Cl H Me Bu-t OMe

 D-148 3. 4-Cl H Et Et OMe

D-149 3, 4-Cl. H Me Bu-t NH ₂

(Table 23)

(表 24)

(Table 24)

化合物 C一 42、 化合物 C一 43、 化合物 C— 1 96、 化合物 C— 1 97、 化 合物 C— 1 98及び化合物 C - 1 99はそれぞれ光学活性体であり、 比旋光度は それぞれ [a] _D ^{2 2} =+ 3 2. 7° ( c = 0. 5 , C H C 1 ₃ ) s [ a 3 D 2 =— 27. 3。 （c = 0. 5, CHC 1 g) . [a] _D ^ ² = + 9. 8。 ( c = 1. 0, C HC 1 ₃ ) 、 [a] _D " ² =+ 2 3. 4° (c = l . 0， CHC 1 g) , [a _D ^{2 2} =- 8. 4。 (c = 1. 0， CHC 1 3) , [a] _D " ² =- 1 9. 9。 （c = l. 0, CHC 1 。） である。

Compound C-42, Compound C-43, Compound C-196, Compound C-197, Compound C-198 and Compound C-199 are optically active substances, respectively. Each ^{_{[a] D 2 2 = +}} 3 2. 7 ° (c = 0. 5, CHC 1 3) s [a 3 D 2 = - 27. 3. (C = 0.5, CHC 1 g). [A] _D ^ ² = +9.8. (C = 1. 0, C HC 1 3), [a] D "2 = + 2 3. 4 ° (c = l 0, CHC 1 g.), [A D 2 2 = - 8. 4. ( c = 1.0, CHC 13), [a] _D " ² =-19.9. (C = l. 0, CHC 1).

 Compound C-16, Compound C-17, Compound C-18, Compound C-21, Compound C-24, Compound C-27, Compound C-34, Compound C_39, Compound C-

47, compound C-51, compound C-54, compound C-62, compound C-66, compound C-71, compound C-73, compound C-75, compound C-81, compound C one

88, Compound C-92, Compound C-94, Compound C-99, Compound C-102, Compound C-106, Compound C-108, Compound C-112, Compound C-114, Compound C — 117, Compound C-122, Compound C-129, Compound C—131, Compound C—140, Compound C—157, Compound C-161, Compound C-165, Compound C 1 169, Compound C-171, Compound C-174, Compound C-177, Compound C-179, Compound C-181, Compound C-184, Compound C-187, Compound C-189, Compound C-1 193, Compound C-196, Compound C-1 198, Compound C-200, Compound D-40, Compound D-63, Compound D-91, Compound D-119, Compound E-30, and Compound E — 37 is diastereomer A, compound C-19, compound C-22, compound C-25, compound C-28, compound C135, compound C-40, compound C-48, compound C One 5 two , Compound C-

55, compound C-63, compound C-67, compound C-72, compound C-74, compound C-76, compound C-82, compound C-89, compound C-93, compound C-1

95, Compound C-100, Compound C-103, Compound C-107, Compound C-

109, compound C—113, compound C—115, compound C—118, compound C—123, compound C—130, compound C—141, compound C—158, compound C

162, Compound C-166, Compound C-170, Compound C-172, Compound C-

1 75, Compound C-178, Compound C-180, Compound C-1 182, Compound C-1

185, Compound C—188, Compound C—190, Compound C—19.4, Compound C—

1997, Compound C—199, Compound C-201, Compound D—41, Compound D— 64, Compound D-92, Compound D-1220, Compound E-31 and Compound E-38 are diastereomers B. Other compounds having two or more asymmetric carbon atoms are diastereomeric mixtures.

 The diastereomer A is a low-polar diastereomer separated by silica gel column chromatography or liquid chromatography, and the diastereomer B is a high-polar diastereomer similarly separated.

 The compound of the present invention represented by the general formula (1) can be produced, for example, according to the following production method.

Manufacturing method 1

 (1)

 1 2

(Wherein, RRR, R ⁴ , X, Y, Z, Q and n represent the same meaning as described above.)

 The compound (1) of the present invention is represented by the general formula (3) using a phenylalkanoic acid derivative represented by the general formula (2) in the presence of a catalyst and / or a base, if necessary, using a condensing agent. It can be produced by reacting with amines.

This reaction is usually performed in a solvent. As a solvent that can be used, any solvent that does not inhibit the reaction may be used.Examples include pentane, hexane, heptane, cyclohexane, petroleum ether, rigoin, hydrocarbons such as benzene, toluene, xylene, dichloromethane, dichloromethane, Halogenated hydrocarbons such as dichloroethane, chloroform, carbon tetrachloride, carbon benzene, and dichlorobenzene; ethers such as ethyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, and dioxane; acetone; Ketones such as methyl ethyl ketone, methyl isobutyl pyrketone, methyl isobutyl ketone, methyl acetate, ethyl acetate Or non-protonic polar solvents such as dimethylsulfoxide, N, N-dimethylformamide, sulfolane, or solvents selected from these. Can be used.

 Examples of the condensing agent include: 1-ethyl-3- (3-dimethylaminopropyl) rubodiimid hydrochloride, N, N'-dicyclohexylcarbodiimide, carbonyl diimidazole, 2-chloro-1,3-dimethyl And imidazolium chloride.

 Examples of the catalyst include 4-dimethylaminopyridine, 1-hydroxybenzotriazole, dimethylformamide and the like.

 As the base, those generally used in this type of reaction can be used. For example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, and alkali metal carbonates such as sodium carbonate and potassium carbonate Or tridimethylamine, trimethylamine, N, N-dimethylaniline, pyridine, N-methylbiperidine, 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), 1,8-diazabicyclo [5 4.0]-7-Pendecene (DBU) and the like, and preferably tertiary amines such as triethylamine, pyridine and N-methylbiperidine. The reaction temperature ranges from 50 ° C to 150 ° C, preferably from 0 ° C to 60 ° C. It is performed in the range of C. The reaction time is preferably 1 to 30 hours.

 Next, a method for producing a starting compound used in this production method will be described.

 The compound represented by the general formula (2) can be produced, for example, by hydrolyzing phenylmalonates with alkali, heating and decarboxylating. This is a known method [Journal of Organic Chemistry, Vol. 13, p. 763 (1948), Organic Syntheses, Vol. 3, 557 (1955), JP-A-40-7491 or Synthesis, 6, 456 (1982)].

Compounds represented by the general formula (3) include, for example, ketones and sodium cyanide. It can be manufactured by the Strecker method from a mixture of aluminum and ammonium chloride. This is a well-known method [Organic Syntheses, Vol. 3, pp. 88 (1955), Journal of Medicinal Chemistry. of Medicinal Chemistry), Vol. 9, pp. 911 (1966) or Tetrahedron Letters, Vol. 17, pp. 1445 (1977) ].

Manufacturing method 2

 Three

 (In the formula, R R 2 R R X, Y, Z, Q and η represent the same meaning as described above, and L represents a halogen atom.)

 The compound (1) of the present invention can be produced by reacting a phenylalkanoic acid halide represented by the general formula (4) with an amamine represented by the general formula (3) in the presence of a base. Can be.

This reaction is usually performed in a solvent. Solvents that can be used may be any solvents that do not inhibit the reaction, for example, pentane, hexane, heptane, cyclohexane, petroleum ether, rig-mouth, hydrocarbons such as benzene, toluene, xylene, and dichloromethane. Halogenated hydrocarbons such as dichloroethane, chloroform, carbon tetrachloride, carbon benzene, dichlorobenzene, ethers such as dimethyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, and dioxane; Ketones such as acetone, methylethyl ketone, methyl isobutyl pyrketone, and methyl isobutyl ketone; acetates such as methyl acetate and ethyl acetate; and nitrites such as acetonitrile and propionitrile Rils or Ν, Ν-dimethylforma An aprotic polar solvent such as mid or sulfolane or a mixed solvent obtained by combining solvents selected from these may be used. As the base, those generally used in this type of reaction can be used. For example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, and alkali metals such as sodium carbonate and potassium carbonate Carbonates, or triethylamine, trimethylamine, N, N-dimethylanilinine, pyridine, N-methylbiperidine, 1,5-diazabicyclo [4.3.0] non-15-ene (DBN), 1 And organic bases such as 8-, diazabicyclo [5.4.0] -7-indene (DBU), and preferably tertiary amines such as triethylamine, pyridine and N-methylbiperidine. The reaction is carried out at a temperature ranging from −50 ° C. to 150 ° C., preferably from 0 ° C. to 60 ° C. The reaction time is preferably up to 30 hours.

 Next, a method for producing a starting compound used in this production method will be described.

 The phenylalkanoic acid halide represented by the general formula (4) is obtained by converting the phenylalkanoic acid represented by the general formula (2) produced by the above-mentioned method into, for example, thionyl chloride, phosphorus pentachloride, It can be produced by reacting with a halogenating agent such as phosphorus tribromide.

Manufacturing method 3

 (1-2)

(In the formula, R ¹ R ² , R ³ , R ⁴ , X, Y, Z and n have the same meaning as described above, and R represents a C 丄 to C ₆ alkyl group.)

 A compound of the present invention represented by the general formula (1-1) which is saturated with hydrogen chloride.

The compound of the present invention represented by the general formula (1-2) can be produced by reacting with the alcohol represented by the formula (5). This reaction is usually performed in a solvent. Any solvent can be used as long as it does not inhibit the reaction.Examples include alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, pentane, hexane, heptane, cyclohexane, petroleum ether, and rig ports. Hydrocarbons such as benzene, toluene, xylene, etc., halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, chlorobenzene, dichlorobenzene, etc., getyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahi Solvents such as ethers such as drofuran and dioxane and mixed solvents obtained by combining solvents selected from these can be used.

 The reaction is carried out at a temperature ranging from −50 ° C. to 150 ° C., preferably from 0 ° C. to 120 ° C. The reaction time is preferably 1 to 20 hours.

 [Best Mode for Carrying Out the Invention]

 Next, a method for producing the compound of the present invention will be specifically described.

Production Example 1 Production of N— (1-cyano-1,2-dimethylpropyl) —2- (4-biphenyl) acetamide (Compound No. A-87)

 Dissolve 1.0 g (4.5 mimol) of 4-biphenylacetic acid in 5 Om1 of dichloromethane and add 1 g (5-dimethylaminopropyl) carbodiimide hydrochloride 1.1 g (5 (0.7 mmol) at room temperature and stirred for 10 minutes. To this mixture was added 0.5 g (4.7 mmol) of 2-amino-1,2,3-dimethylbutyronitrile, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, water was added to the reaction solution, the dichloromethane layer was washed with water, dried over anhydrous magnesium sulfate, and then dichloromethane was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.1 g (yield: 76%) of the desired product having a melting point of 151-152 ° C.

Production Example 2 Production of N- (1-cyano 1,2-dimethylpropyl) —2- (4-bromophenyl) propionamide (Compound Nos. C-47 and C-48) 2-tetrafuran in 20 ml of tetrahydrofuran 0.9 g (8.0 mimol) of 1,2-dimethylbutyronitrile and 0.8 g (7.9 mimol) of triethylamine were dissolved. Under stirring at 10 ° C., 1.5 g (6.0 mmol) of 2- (4-bromophenyl) propionyl chloride was added dropwise to the mixture over 5 minutes. After dropping, The reaction was stirred at room temperature for 5 hours. The reaction solution was concentrated, water was added, and extracted with ethyl acetate. After the ethyl acetate layer was dried over anhydrous magnesium sulfate, ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.45 g (yield: 24%) of diastereomer A (low-polar form) having a melting point of 130 to 131 ° C, and a melting point of 121-123 °. 0.75 g (yield: 40%) of diastereomer B of C (highly polar form) was obtained.

Production Example 3 Production of N- (1-carbamoyl-1-ethylpropyl) -1- (4-chlorophenyl) propionamide (Compound No. D-32)

 2.3 g (18 mmol) of 2-amino-2-ethylbutylamide and 2.0 g (20 mmol) of tritylamine were suspended in 5 Om.l of tetrahydrofuran. Under stirring at room temperature, 1 Om 1 of a tetrahydrofuran solution in which 3.0 g (15 mmol) of 2- (4-chlorophenyl) propionic chloride was dissolved was added dropwise to the suspension over 10 minutes. After the addition was completed, the reaction solution was further stirred at room temperature for 3 hours. The reaction solution was concentrated, water was added, and the mixture was extracted with black-mouthed form. After drying the layer at the mouth, the dried form was distilled off under reduced pressure. The obtained crystals were washed with diisopropyl ether to give 4.2 g (yield 94%) of the desired product having a melting point of 116 to 118 ° C.

Production Example 4 Production of methyl 2- (1- (4-chlorophenyl) ethylcarbonylamino) -12-ethylbutylate (Compound No. D-28)

 0.6 g (2.0 mimol) of N- (1-carboxymethyl-1-ethylpropyl) -1- (4-chlorophenyl) propionamide obtained from Production Example 3 in 1 Oml of hydrogen chloride saturated methanol ) Was dissolved, and the mixture was stirred under reflux for 3 hours. After the reaction solution was concentrated, water was added, and the mixture was extracted with ethyl acetate. After the ethyl acetate layer was dried over anhydrous magnesium sulfate, the ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.5 g (yield 81%) of the desired product having a melting point of 98 to 99 ° C.

Production Example 5 Production of N- (1-cyano-1-cyclopropylethyl) 1-2- (4-cyclophenyl) -2-methylpropionamide (Compound No. E-9)

2-Amino-2-cyclopropylpropionate in 20 ml of tetrahydrofuran 0.25 g (2.3 mimol) of ril and 0.3 g (3.0 mimol) of triethylamine were dissolved. To this mixture, 0.5 g (2.3 mmol) of 2- (4-chlorophenyl) -2-methylpropionic chloride was added dropwise at 10 with stirring over 5 minutes. After the addition was completed, the reaction solution was stirred at room temperature for 3 hours. After the reaction solution was concentrated, water was added, and the mixture was extracted with ethyl acetate. After the ethyl acetate layer was dried over anhydrous magnesium sulfate, ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.5 g (yield: 75%) of the desired product having a melting point of 93 to 94 ° C. Production Example 6 Production of isopropyl 2- (4-trifluoromethylbenzylcarbonylamino) -1,2,3-dimethylbutyrate (Compound No. B-36)

 In 50 ml of dichloromethane was dissolved 1.0 g (4.9 mimol) of 4-trifluoromethylvinylacetic acid, and the mixture was dissolved in 1-ethyl-3- (3-dimethylaminobutanol) carbodiimide. Hydrochloride (1.1 g, 5.7 mmol) was added at room temperature, and the mixture was stirred for 10 minutes. 0.9 g (5.2 mmol) of isopropyl 2-amino-2,3-dimethylbutyrate was added to this mixture, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, water was added to the reaction solution, the dichloromethane layer was washed with water, dried over anhydrous magnesium sulfate, and then dichloromethane was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.4 g (yield: 80%) of the desired product having a melting point of 122 to 23 ° C.

 The fungicide for agricultural and horticultural use of the present invention comprises a fungicil derivative of the general formula [I] as an active ingredient. When the compound of the present invention is used as an agricultural and horticultural fungicide, the active ingredient can be used in an appropriate dosage form depending on the purpose. Normally, the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, a surfactant or the like may be added to the active ingredient, and used in the form of powders, wettable powders, emulsions, granules and the like.

Suitable carriers include, for example, solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea, isopropyl alcohol, xylene, cyclohexanone, and methyl naphthalene. And the like. Examples of surfactants and dispersants include dinaphthyl methanesulfonate, alcohol sulfate, alkylaryl sulfonate, lignin sulfonate, polyoxyethylene glycol ether, and polyoxyethylene glycol ether. Polyalkylene alkylaryl ether, polyoxoxylene sorbitan monoalkylate, and the like. Examples of the auxiliary include carboxymethylcellulose and the like. These preparations are diluted to an appropriate concentration and sprayed or applied directly.

 The fungicide for agricultural and horticultural use of the present invention can be used by foliage application, soil application or water surface application. The mixing ratio of the active ingredient is appropriately selected according to need, but is preferably 0.1 to 20% (weight) for powders and granules, and 5 to 80% (weight) for emulsions and wettable powders. It is.

 The application rate of the agricultural and horticultural fungicide of the present invention varies depending on the type of the compound used, the target disease, the tendency to occur, the degree of damage, the environmental conditions, the dosage form used, and the like. For example, when used as such as powders and granules, the active ingredient may be appropriately selected from the range of 0.1 g to 5 kg per 10 ares, preferably lg to 1 kg. When used in liquid form such as emulsions and wettable powders, it is appropriate to appropriately select from the range of 0.1 ppm to 10,000 ppm, preferably 10 to 3, and OOO ppm.

 The compound according to the present invention, by the above-mentioned application form, inhibits plant diseases caused by bacteria belonging to algae (Oomycetes), ascomycetes (Ascomycetes), incomplete fungi (Deuteromycetes), algae (Oomycetes) and basidiomycetes (Basidiomycetes). Can be controlled.

 Next, specific bacterial names are given as non-limiting examples. The genus Pyricularia (eg, Pyricularia oryzae), the genus Sphaerotheca (eg, Sphaerotheca fuliginea), the genus Venturia (eg, Venturia inaequalis), the genus Gypella (eg, Giberella) Botrytis (Botrytis) genus, such as Botrytis cinerea, Alternaria (Alternaria) genus, such as Komatsuna black soot (A ernaria brassicicola), Rhizoctonia ¾, For example, Rhizoctonia solani, Puccinia genus, such as rust 病 (Puccinia recondita li, Pseudoperonospora ¾), and pheasant 囷 (Pseudoperonospora cubensis li).

Further, the compound of the present invention may be mixed with an insecticide, other fungicides, herbicides, plant growth regulators, fertilizers and the like, if necessary. Next, representative production of the agricultural and horticultural fungicide of the present invention. The formulation method will be specifically described with reference to examples of agents. In the following description, “%” indicates weight percentage.

Formulation Example 1 Powder

 Compound (A-4) 2%, diatomaceous earth 5% and clay 93% were uniformly mixed and pulverized to obtain a powder.

Formulation Example 2 wettable powder

 A wettable powder was prepared by uniformly mixing and pulverizing 50% of the compound (B-16), 45% of diatomaceous earth, 2% of sodium dinaphthylmethanedisulfonate and 3% of sodium ligninsulfonate.

Formulation Example 3 Emulsion

 An emulsion was prepared by uniformly dissolving 30% of compound (C-29), 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzenesulfonate and 35% of methylnaphthalene.

Formulation Example 4 Granules

 A compound (B-34) 5%, sodium salt of lauryl alcohol sulfate 2%, sodium ligninsulfonate 5%, carboxymethyl cellulose 2% and clay 86% are uniformly mixed and ground. 20 parts by weight of water was added to 100 parts by weight of this mixture, kneaded, processed into granules of 14 to 32 mesh using an extrusion granulator, and then dried to obtain granules.

 Next, the effects of the agricultural and horticultural fungicide of the present invention will be specifically described with reference to test examples. In the test, the following compounds described in JP-A-6-220004 were used as comparative drugs.

 Comparative drug: N— (1—cyano—1-cyclopropylethyl) —2— (2,4—dichlorophenyl) acetamide

Test example 1 Rice blast prevention effect test

Approximately 15 rice seeds (variety: Asahi Aichi) were sown in a clay pot with a diameter of 7 cm and cultivated in a greenhouse for 2 to 3 weeks. A hydration agent prepared according to Preparation Example 2 was diluted with water so that the active ingredient concentration became 500 ppm, and sprayed 10 ml per pot onto a rice seedling in which the fourth leaf had completely developed. After air-drying, a conidia suspension of rice blast (Pyricularia oryzae) is sprayed and inoculated. Immediately for 24 hours in a humidity chamber at 25 ° C. After that, they were transferred to a greenhouse and the number of lesions on the fourth leaf was examined 5 days after inoculation. The control value was determined by Equation 1, and the results of evaluation based on the criteria in Table 25 are shown in Tables 26 to 28.

 (Number 1)

Number of lesions in the treatment area

 Control value (%) 1 x 100

 Lesion count in untreated area

(Table 25) Evaluation control value

 A 100%

 B 80% or more and less than 100%

 C 50% or more and less than 80%

D less than 50%

(Table 26)

(表 27)

(Table 27)

(表 2 8 ) 化合物番号 評価 化合物番号 評価

(Table 28) Compound number evaluation Compound number evaluation

C-180 B D-63 B

C-18 1 A D- 64 A

C-182 A • D- 65 B

C-184 B D-73 A

C-185 B D-76 B

C-1 86 B D-9 1 A

C-187 A D-92 A

C-188 B D-99 B

C- 189 A D-104 B

C- 190 A D- 105 B

C-19 1 A D-1 19 A

C-192 B D- 120 B

C-193 B E-7 B

C-194 B E-8 B

C-195 B E-9 A

C- 196 A E- 1 1 B

C-197 A E-18 A

C-198 A E-32 B

C-199 A E-33 A

C-200 B E- 34 A

C-20 1 B E-37 B

C-202 B E-38 B

D- 19 A

 D-20 A

 D-21 A

 D-26 A

 D-28 A

 D-29 A

 D-32 A

 D-34 B

 D-39 A

 D-40 A

 D-4 1 A

 D-42 A

D- 59 B Test example 2 Rice blast surface application test

Rice seedlings at the 2 leaf stage (variety: Asahi Aichi) were transplanted to a 9 cm diameter white porcelain pot in three greenhouses with three stems each. At the 3 leaf stage, the pots were subjected to water application so that the granules prepared according to Formulation Example 4 would have an active ingredient concentration of 300 g per 10 ares. When the fourth leaf of the rice seedling was completely developed, a conidia suspension of rice blast fungus (Pyricularia oryzae) was spray-inoculated and immediately left standing in a humidity chamber at 25 ° C for 24 hours. Then, the rice seedlings were transferred to a greenhouse to cause disease. Five days after inoculation, the number of lesions on the fourth leaf was examined. The control value was calculated using Equation 1, and the results evaluated according to the criteria in Table 25 are shown in Table 29.

(Table 29)

試験例 3 リ ンゴ黒星病予防効果試験

Test example 3 Lingual scab prevention test

 Four plastic seedlings (variety: Kodama) were sown in 5.5 cm diameter plastic pots and grown in a greenhouse for 20 days. When the fourth leaf of the true leaves of the apple seedlings was completely developed, the wettable powder prepared according to Preparation Example 2 was diluted with water so that the active ingredient concentration became 50 ppm, and 20 ml per pot was sprayed. After the drug solution attached to the apple seedlings was dried, a spore suspension of apple scab (Venturia inaequalis) was inoculated by spraying, and immediately allowed to stand in a humidity chamber at 20 ° C for 48 hours. Then, the apple seedlings were transferred to a greenhouse to cause disease, and 14 days after inoculation, the diseased area of each true leaf was investigated. The disease severity was evaluated based on the criteria shown in Table 30, and from the disease severity and the corresponding number of leaves, the damage was determined using Equation 2, and the control value was calculated using Equation 3. The resulting control values were evaluated based on the criteria in Table 25, and the results are shown in Table 31.

(Table 30)

(Equation 2)

∑ (Severity X number of leaves)

 Damage (%) X 1 0 0

 Number of survey leaves X 4

(Equation 3)

Damage of treatment area

 Control value (%) X 100

Damage of untreated area (Table 31)

Claims

 The scope of the claims  General formula (1),

[In the formula, R ¹ represents a hydrogen atom or a C -C ₆ alkyl group, R ² represents a hydrogen atom, C. 1 to ^C 6 alkyl group, C ₀ -C consequent opening alkyl or C] -C ₄ Haroaruki Le group the stands, R ³ and R ⁴ are each independently C丄-C ₆ alkyl group, C ₀ ~ c ₆ alkenyl group, c ₃ -C ₆ cycloalkyl group, C ₀ ~ C c alkoxyalkylene group or C丄Represents a C ₄ -C ₄ alkyl group, or R ³ and R ⁴ together with the carbon atom to which they are attached are a 5- to 7-membered cycloalkyl group, which is substituted by a C 1 -C 4 alkyl group. Q represents a cyano group or a group of COR ⁵ (R ⁵ is a hydroxy group, C, ~ C. Alkyl group, C j Ce alkoxy group, c ₂ -C haalkenyloxy group, C ₂ -C alkynyloxy group, C. ~ CP cycloalkyloxy group, Represents a phenoxy group, a benzyloxy group, an amino group, a dialkylamino group or a C to C dialkylamino group.), And X represents a halogen atom, a CC ealkyl group, or a c-c alkenyl group. , c ₂ to c ₆ alkynyl group, c ₃ to c ₆ cycloalkyl group, C to c haloalkyl group, arsenate Dorokishi group, c ₁ to c ₆ alkoxy group, c ₂ ~ c ₆ Arukeniruokishi group, c ₂ ~ c ₆ alkynyloxy group, c ₃ -C cycloalkyloxy group, C i C haloalkoxy group, aryloxy group (the group is a C ₆ to ₆ alkyl group, c ₁ to ₄ haloalkyl group, C i C e By an alkoxy, cyano, nitro or halogen atom May be conversion.) Substituted heteroaryl § reel O alkoxy (in which the group Ci～c ₆ alkyl le groups, C, C haloalkyl groups, C丄~c alkoxy group, Shiano group, nitro group or halogen atom It may be.), Ji ~. Alkylthio O group, C to c alkylsulfinyl group, Ci～c ₆ alkylsulfonyl groupヽC j~c ₄ haloalkylthio group, § Li one thio group (said group ci ~ C e alkyl group, Ci～c ₄ Alkyl groups, alkoxy groups, cyano groups, nitro groups Or it may be substituted by a halogen atom. ), A heteroarylthio group (the group may be substituted by a C ₁ -C ₆ alkyl group, a C 1 -C ₄ haloalkyl group, a C i C g alkoxy group, a cyano group, a nitro group or a halogen atom) There.), § reel sulfinyl group (said group C i~C ₆ alkyl group, C i~C ₄ Ha port alkyl group, C -C alkoxy group, Shiano group, optionally substituted by nitro group or a halogen atom good.) substituted, § Li one Rusuruhoniru (in which the group C丄-C ₆ alkyl group, C -C Ha port alkyl group,.丄~. Haarukokishi group, Shiano group, by a two-Bok port group or a halogen atom ), An amino group, a C j -c ₆ alkylamino group, a ci-c haalkylalkylamino group, a nitro group, a cyano group, a peryl group (the group is a C ₁ -C ₆ alkyl group) , A C j -C haloalkyl group, ^C. 1 to ^C 6 alkoxy group, Shiano group, may be substituted by nitro group or a halogen atom. ), A heteroaryl group (the group may be substituted by a C i -C _ff alkyl group, a C ₁ -haloalkyl group, a c ₁ -c ₆ alkoxy group, a cyano group, a nitro group or a halogen atom.), An aralkyl A group (the group may be substituted by a C 1 to C ₆ alkyl group, a C, to C ₄ haloalkyl group, a C i to C ₆ alkoxy group, a cyano group, a nitro group or a halogen atom); C-c alkylcarbonyl group, arylcarbonyl group (the group may be substituted by a C, -C alkyl group, a _4- alkyl group, a CJCP alkoxy group, a cyano group, a nitro group or a halogen atom) .), hetero § reel carbonyl group (said group C J～c. alkyl group, ci ~ c ₄ c port alkyl group, c ₁ to c ₆ alkoxy group, Shiano group, optionally substituted by nitro group or a halogen atom Good ), Represents a formyl group or a C j ~ c ₆ alkoxycarbonyl two Le group, Y and Z are each hydrogen atom, C Ce alkyl group, c to c haloalkyl group, C i Ce alkoxy group, Shiano group, a nitro group, or Represents a halogen atom, and n represents an integer of 0 to 3. However, when R ¹ and R ² simultaneously represent a hydrogen atom, Y and Z both represent a hydrogen atom, and n represents an integer of 1 to 3. A phenylalkanoic acid amide derivative represented by the formula: 2. General formula (1),

[In the formula, R ¹ represents a hydrogen atom or a C -C ₆ alkyl group, R ² represents a hydrogen atom, C 1 through C 6 alkyl group, C ₃ -C Ha cycloalkyl group or C ₁ -C _lambda Haroaruki Le group Wherein R ³ and R ⁴ are each independently a C 丄 to C ₆ alkyl group, a C ゥ to C ₆ alkenyl group, or C. Or a C j -C ₄ haloalkyl group, or R ³ and R ⁴ are a 5- to 7-membered cycloalkyl group together with the carbon atom to which they are attached (the group is a C to C _And Q may be a cyano group or a group of COR ⁵ (R ⁵ is a hydroxy group, a C ₁ -C ₆ alkyl group, a CCP alkoxy group, a C ₂ -C alkenyl) Oxy group, C ₂ -C ₆ alkynyloxy group, C ₃ -c cycloalkyloxy group, phenoxy group, benzyloxy group, amino group, CC g alkylamino group or C, C ₆ -dialkylamino group X represents a halogen atom, a C, -C p alkyl group, a C ₂ -C ₆ alkenyl group, or C. ~ C ₆ alkynyl group, CO ~ CP cycloalkyl group, c 丄 ~ c ₄ alkyl group, hydroxy group, c, ~ c ₆ alkoxy group, c ₂ ~ c ₆ alkenyloxy group, C. ~c Ha alkynyl O carboxy group, c ₃ ~ c ₆ cycloalkyl O alkoxy group, C i ~ C 4 alkoxy group.丄~ Ji lower alkylthio group substituted, § Li one Ruokishi (in which the group c ₁ to c ₆ alkyl group, ci ~ c ₄ c port alkyl group, C i C ^ alkoxy group, Shiano group, nitro group or halogen atom . which may be), the hetero § reel O alkoxy (in which the group C: ~ c ₆ alkyl group, Ci～c ₄ Ha port alkyl group, C i C g alkoxy group, Shiano group, two preparative port group or by halogen atoms which may be substituted.), cj~c ₆ alkylthio group, ci ~ c ₆ alkylamino amino group, c丄to c ₆ dialkyl amino group, two preparative port group, Shiano group, Ariru (in which the group the c ₂ to c ₆ alkyl group, c ₁ ~ 4 C port alkyl group, C i ~ C Haarukokishi group, Shiano group, may be substituted by a nitro group or a halogen atom.), Heteroariru group, Ararukiru group , c, to c _e alkylcarbonyl group, Honoremiru group, § reel carbonyl group, a hetero丄b  An arylcarbonyl group or a ci-Calkoxycarbonyl group, and Y and z are a hydrogen atom, a CiCe alkyl group, a c-c haloalkyl group, ~ C represents an alkoxy group, a cyano group, a nitro group or a halogen atom, and n represents an integer of 0-3. However, when R ¹ and R represent a hydrogen atom at the same time, Y and Z both represent a hydrogen atom, and n represents an integer of 1-3. A phenylalkanoic acid amide derivative represented by the formula:  3. General formula (1),

[Wherein, R ¹ represents a hydrogen atom or a C ₆ alkyl group, R ² represents a hydrogen atom or a C 1 -C 6 alkyl group, and R ³ and R ⁴ each independently represent a C j -C alkyl group. , C Ri ~ C alkenyl group, or represents C ₃ to c ₆ cycloalkyl group or a C j~C ₄ haloalkyl group, or R. And R ⁴ represents a cycloalkyl group having 5-membered to 7-membered ring together with the carbon atom bonded, Q is Shiano group or groups one C OR "(R" is human Dorokishi group, C _chi ~ C ₆ alkoxy group, amino groups, C丄~C Arukiruamino group or C I～C represents a dialkyl § amino group.) represents, X is a halogen atom, ^C 1 ~ ^C 6 alkyl groups, C ₂ ~ C ₆ alkynyl groups, C i ~ C Haloalkyl group, hydroxy group, C ·! ~ C ₆ alkoxy group, C, ~ C ₄ haloalkoxy group, aryloxy group (the group is a C i -C alkyl group, a C -C ₄ haloalkyl group , A -C ₆ alkoxy group, a cyano group, a nitro group, or a halogen atom.), A heteroaryloxy group (C _λ -C ₆ alkyl group, C ₁ -C ₄ haloalkyl group, CC g substituted by an alkoxy, cyano, nitro, or halogen atom Or.), C to c ₆ alkylthio group, c ₁ ~ c ₄ haloalkylthio group, Ci～c ₆ dialkylamino group, a nitro group, Shiano group, Ryo aryl group (said group c ₁ to c ₆ alkyl group, c ₁ to c ₄ c port alkyl group, CJCP substituted by alkoxy, cyano, nitro or halogen atom It may be. ), Ci-c ₆ alkylcarbonyl group, arylcarbonyl group or heteroarylcarbonyl group, Y and Z each represent a hydrogen atom or a halogen atom, and n represents an integer of 0-3. However, when R ¹ and R ² simultaneously represent a hydrogen atom, Y and Z both represent a hydrogen atom, and n represents an integer of 1 to 3. A phenylalkanoic acid amide derivative represented by the formula: 4. General formula (1),

[Wherein, R i represents a hydrogen atom, R ² represents a hydrogen atom or a C i -C ₆ alkyl group, R ³ and R ⁴ each independently represent a C 丄 -C alkyl group, C ₂ -CP Aruke alkenyl group, C ₃ -C Ha cycloalkyl group or C丄-C ₄ Ha port alkyl or a group, or R ³ and R ⁴ are cycloalkyl Le group 5- to 7-membered ring together with the carbon atom bonded And Q represents a cyano group or a group —COR ⁵ (R ″ represents a C 丄 -C ₆ alkoxy group or an amino group.), X represents a halogen atom, a C i -C p alkyl group, a C c ₆ alkynyl groups, C丄-C ₄ Ha port alkyl groups, C i C Haarukokishi groups, C j -C haloalkoxy group, Fuwenokishi (in which the group C _l ~ C p alkyl groups, C _chi ~ C ₄ C Alkyl group, C: may be substituted by a C ₆ -alkoxy group or a halogen atom.), A C ₆ -C ₆ alkylthio group, a C 1 -C e dialkylamino Group, the two Bok port group, Shiano group, Fuweniru (in which the group Ci～c ₆ alkyl group, c ₁ ~ It may be substituted by a C haloalkyl group, a C, -C alkoxy group or a halogen atom. ) Represents a ci-c ₆ alkylcarbonyl group or a benzoyl group, Y and Z both represent a hydrogen atom, and n represents an integer of 1-3. ] A phenylalkanoic acid amide derivative represented by the formula: -General formula (1),

[Wherein, R ¹ represents a hydrogen atom, R ² represents a hydrogen atom or a C-C ₆ alkyl group, and R and R ⁴ each independently represent a C j-C ₆ alkyl group, C ₂ -C ₆ 7 represents a alkenyl group, a C-C cycloalkyl group or a C- ₄ alkyl group, or R ³ and R ⁴ are a 5- to 7-membered cycloalkyl group together with the carbon atom to which they are bonded. the stands, Q represents a Shiano group or a group -COR ⁵ (R ⁵ represents a C i~C ₆ alkoxy group or Amino group.), X is a halogen atom, C -C alkyl group, _C? ~ C alkynyl group, C i-C haloalkyl group, C C P alkoxy group, It represents C丄-C ₄ Ha port alkoxy group, phenoxy group, C丄-C ₆ alkylthio group, Ji丄-C ₆ dialkyl § amino group, a nitro group or a Fuweniru group, Y and Z together represent water atom, n represents an integer of 1 to 3. A phenylalkanoic acid amide derivative represented by the formula:  6. A fungicide for agricultural and horticultural use containing the phenylalkanoic acid amide derivative according to claim 1, claim 2, claim 3, claim 4, or claim 5 as an active ingredient.  7. General formula (2),

(Wherein, R ¹ R ² , X, Y, Ζ, and η represent the same meaning as in claim 1) and a phenylalkanoic acid derivative represented by the general formula (3),

H ₂ NCQ (3)  R4 (Wherein, R ³ , R ⁴ and Q have the same meanings as in claim 1). The phenylalkanoic acid derivative according to claim 1 is reacted with an amine derivative represented by the following formula: Manufacturing method. 8. General formula (4),

(Wherein, R ¹ R ² , X, Y, Ζ, and η have the same meanings as in claim 1 and L represents a halogen atom.) A phenylalkanoic acid halide derivative represented by the general formula (3) ), R3 H ₉ NCQ (3)  R4 (Wherein, R ³ , R ⁴ and Q have the same meaning as in claim 1). The phenyl alkanoic acid derivative according to claim 1, which is reacted with an amine derivative represented by the following formula: Manufacturing method.